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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3360
https://doi.org/10.1107/S1600536810049470

(E)-N′-(2,4-Di­chloro­benzyl­­idene)-3-nitro­benzohydrazide

Fu-Lin Maoa* and Chun-Hua Daia

aJiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection, Department of Chemistry, Yancheng Teachers University, Yancheng 224002, People's Republic of China
*Correspondence e-mail: xpzhougroup@163.com

(Received 25 November 2010; accepted 26 November 2010; online 30 November 2010)

The title compound, C14H9Cl2N3O3, was prepared by the reaction of 3-nitro­benzohydrazide with 2,4-dichloro­benzalde­hyde. The mol­ecule adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.6 (2)°. In the crystal, the hydrazone mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010[Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.]); Zhang et al. (2010[Zhang, Y.-H., Zhang, L., Liu, L., Guo, J.-X., Wu, D.-L., Xu, G.-C., Wang, X.-H. & Jia, D.-Z. (2010). Inorg. Chim. Acta, 363, 289-293.]); Angelusiu et al. (2010[Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055-2062.]). For related structures, see: Huang & Wu (2010[Huang, H.-T. & Wu, H.-Y. (2010). Acta Cryst. E66, o2729-o2730.]); Khaledi et al. (2010[Khaledi, H., Alhadi, A. A., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o105-o106.]); Zhou & Yang (2010[Zhou, C.-S. & Yang, T. (2010). Acta Cryst. E66, o290.]); Ji & Lu (2010[Ji, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514.]); Singh & Singh (2010[Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172.]); Ahmad et al. (2010[Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022.]). For similar compounds that we have reported recently, see: Dai & Mao (2010a[Dai, C.-H. & Mao, F.-L. (2010a). Acta Cryst. E66, o2942.],b[Dai, C.-H. & Mao, F.-L. (2010b). Acta Cryst. E66, o3004-o3005.]).

[Scheme 1]

Experimental

Crystal data

  • C14H9Cl2N3O3

  • Mr = 338.14

  • Monoclinic, P 21 /c

  • a = 12.004 (3) Å

  • b = 14.384 (3) Å

  • c = 8.465 (2) Å

  • β = 96.302 (2)°

  • V = 1452.8 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.46 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.913, Tmax = 0.921

  • 11555 measured reflections

  • 3163 independent reflections

  • 2128 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.107

  • S = 1.05

  • 3163 reflections

  • 202 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O1i 0.89 (1) 2.04 (2) 2.859 (2) 152 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810049470/sj5069sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049470/sj5069Isup2.hkl

checkCIF report


Comment top

In the last few years, medical applications of a number of hydrazone compounds have been received much attention (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). The structures of several hydrazone derivatives have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on this area (Dai & Mao, 2010a,b), in this paper, we report the structure of the new derivative EN'-(2,4-dichlorobenzylidene)-3-nitrobenzohydrazide.

In the molecule of the title compound, the dihedral angle between the C1···C6 and C9···C14 benzene rings is 4.6 (2)°. The O2/N3/O3 plane forms a dihedral angle of 8.9 (2)° with the C9···C14 benzene ring. The bond lengths and angles are comparable to those found in the hydrazone compounds cited above. In the crystal structure, the hydrazone molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), to form one-dimensional chains along the c axis, as shown in Fig. 2.

Related literature top

For medical applications of hydrazones, see: Ajani et al. (2010); Zhang et al. (2010); Angelusiu et al. (2010). For related structures, see: Huang & Wu (2010); Khaledi et al. (2010); Zhou & Yang (2010); Ji & Lu (2010); Singh & Singh (2010); Ahmad et al. (2010). For similar compounds that we have reported recently, see: Dai & Mao (2010a,b).

Experimental top

The reaction of 3-nitrobenzohydrazide (0.181 g, 1 mmol) with 2,4-dichlorobenzaldehyde (0.174 g, 1 mmol) in 50 ml methanol at room temperature afforded the title compound. Yellow block-shaped single crystals were formed by slow evaporation of the clear solution in air.

Refinement top

The amino H atom was located in a difference Fourier map and refined with N—H = 0.90 (1) Å, and Uiso = 0.08 Å2. Other H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Structure description top

In the last few years, medical applications of a number of hydrazone compounds have been received much attention (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). The structures of several hydrazone derivatives have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on this area (Dai & Mao, 2010a,b), in this paper, we report the structure of the new derivative EN'-(2,4-dichlorobenzylidene)-3-nitrobenzohydrazide.

In the molecule of the title compound, the dihedral angle between the C1···C6 and C9···C14 benzene rings is 4.6 (2)°. The O2/N3/O3 plane forms a dihedral angle of 8.9 (2)° with the C9···C14 benzene ring. The bond lengths and angles are comparable to those found in the hydrazone compounds cited above. In the crystal structure, the hydrazone molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), to form one-dimensional chains along the c axis, as shown in Fig. 2.

For medical applications of hydrazones, see: Ajani et al. (2010); Zhang et al. (2010); Angelusiu et al. (2010). For related structures, see: Huang & Wu (2010); Khaledi et al. (2010); Zhou & Yang (2010); Ji & Lu (2010); Singh & Singh (2010); Ahmad et al. (2010). For similar compounds that we have reported recently, see: Dai & Mao (2010a,b).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atomic numbering.
[Figure 2] Fig. 2. Crystal packing of the title compound, viewed down the b axis. Intermolecular interactions are drawn as dashed lines.
(E)-N'-(2,4-Dichlorobenzylidene)-3-nitrobenzohydrazide top
Crystal data top
C14H9Cl2N3O3F(000) = 688
Mr = 338.14Dx = 1.546 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2237 reflections
a = 12.004 (3) Åθ = 2.3–24.5°
b = 14.384 (3) ŵ = 0.46 mm−1
c = 8.465 (2) ÅT = 298 K
β = 96.302 (2)°Block, yellow
V = 1452.8 (6) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3163 independent reflections
Radiation source: fine-focus sealed tube2128 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −15→13
Tmin = 0.913, Tmax = 0.921k = −18→18
11555 measured reflectionsl = −10→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.1033P]
where P = (Fo2 + 2Fc2)/3
3163 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.22 e Å−3
1 restraintΔρmin = −0.20 e Å−3
Crystal data top
C14H9Cl2N3O3V = 1452.8 (6) Å3
Mr = 338.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.004 (3) ŵ = 0.46 mm−1
b = 14.384 (3) ÅT = 298 K
c = 8.465 (2) Å0.20 × 0.20 × 0.18 mm
β = 96.302 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3163 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2128 reflections with I > 2σ(I)
Tmin = 0.913, Tmax = 0.921Rint = 0.038
11555 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.22 e Å−3
3163 reflectionsΔρmin = −0.20 e Å−3
202 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.26406 (6)−0.09815 (4)0.11977 (8)0.0651 (2)
Cl20.49631 (6)−0.18532 (5)−0.36654 (9)0.0760 (3)
N10.28128 (14)0.18486 (11)−0.03316 (19)0.0344 (4)
N20.23633 (14)0.25093 (11)0.06051 (18)0.0342 (4)
N30.12644 (17)0.66091 (13)0.0801 (3)0.0542 (5)
O10.20635 (13)0.34676 (9)−0.15308 (16)0.0454 (4)
O20.19086 (19)0.67781 (12)−0.0175 (3)0.0808 (6)
O30.06980 (18)0.71959 (12)0.1368 (3)0.0922 (7)
C10.33504 (17)−0.06183 (14)−0.0373 (3)0.0385 (5)
C20.34878 (16)0.03282 (13)−0.0659 (2)0.0330 (5)
C30.40982 (18)0.05744 (14)−0.1909 (2)0.0394 (5)
H30.42010.1200−0.21280.047*
C40.45528 (18)−0.00914 (16)−0.2829 (2)0.0449 (5)
H40.49730.0084−0.36400.054*
C50.43747 (18)−0.10158 (15)−0.2525 (3)0.0446 (6)
C60.37757 (18)−0.12984 (15)−0.1318 (3)0.0451 (6)
H60.3657−0.1926−0.11350.054*
C70.30075 (17)0.10478 (13)0.0282 (2)0.0353 (5)
H70.28470.09230.13110.042*
C80.20044 (16)0.33100 (13)−0.0112 (2)0.0320 (5)
C90.15054 (16)0.40225 (13)0.0894 (2)0.0296 (4)
C100.16380 (16)0.49489 (13)0.0476 (2)0.0340 (5)
H100.20560.5105−0.03470.041*
C110.11400 (18)0.56310 (14)0.1300 (2)0.0386 (5)
C120.05041 (19)0.54271 (16)0.2516 (3)0.0490 (6)
H120.01730.58980.30540.059*
C130.03713 (19)0.45074 (17)0.2916 (3)0.0477 (6)
H13−0.00560.43560.37320.057*
C140.08693 (16)0.38009 (15)0.2110 (2)0.0376 (5)
H140.07740.31830.23880.045*
H20.231 (2)0.2398 (18)0.1627 (14)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0776 (5)0.0440 (4)0.0797 (5)−0.0040 (3)0.0359 (4)0.0085 (3)
Cl20.0832 (5)0.0620 (4)0.0845 (5)0.0183 (4)0.0174 (4)−0.0351 (4)
N10.0418 (10)0.0307 (9)0.0318 (9)0.0035 (8)0.0095 (8)−0.0038 (7)
N20.0493 (11)0.0294 (9)0.0259 (8)0.0063 (8)0.0126 (8)0.0000 (7)
N30.0544 (14)0.0335 (11)0.0733 (15)0.0013 (10)0.0004 (11)−0.0153 (10)
O10.0735 (11)0.0371 (8)0.0285 (8)0.0118 (7)0.0187 (7)0.0037 (6)
O20.1069 (17)0.0392 (10)0.1022 (16)−0.0029 (10)0.0370 (14)0.0029 (10)
O30.0933 (15)0.0387 (10)0.151 (2)0.0116 (10)0.0411 (14)−0.0234 (12)
C10.0363 (12)0.0334 (11)0.0455 (12)0.0019 (9)0.0034 (10)0.0002 (9)
C20.0334 (11)0.0326 (11)0.0324 (11)0.0044 (9)0.0011 (9)−0.0038 (8)
C30.0489 (14)0.0332 (11)0.0365 (12)0.0037 (10)0.0059 (10)−0.0011 (9)
C40.0486 (14)0.0508 (14)0.0365 (12)0.0040 (11)0.0098 (10)−0.0078 (10)
C50.0425 (13)0.0420 (13)0.0484 (13)0.0102 (10)0.0013 (11)−0.0168 (10)
C60.0474 (14)0.0297 (11)0.0568 (14)0.0037 (10)−0.0002 (12)−0.0072 (10)
C70.0415 (13)0.0348 (11)0.0301 (11)0.0036 (9)0.0068 (9)−0.0008 (8)
C80.0382 (12)0.0286 (10)0.0299 (11)−0.0011 (9)0.0066 (9)−0.0021 (8)
C90.0300 (11)0.0327 (11)0.0258 (10)0.0025 (8)0.0024 (8)−0.0012 (8)
C100.0338 (11)0.0334 (11)0.0351 (11)−0.0003 (9)0.0048 (9)−0.0041 (8)
C110.0376 (12)0.0341 (11)0.0426 (12)0.0050 (9)−0.0017 (10)−0.0076 (9)
C120.0478 (14)0.0534 (15)0.0460 (13)0.0155 (11)0.0054 (11)−0.0160 (11)
C130.0452 (14)0.0649 (16)0.0355 (12)0.0095 (12)0.0155 (10)−0.0011 (11)
C140.0391 (12)0.0430 (12)0.0315 (11)0.0030 (10)0.0070 (9)0.0031 (9)
Geometric parameters (Å, º) top
Cl1—C11.736 (2)C4—C51.376 (3)
Cl2—C51.741 (2)C4—H40.9300
N1—C71.275 (2)C5—C61.374 (3)
N1—N21.384 (2)C6—H60.9300
N2—C81.350 (2)C7—H70.9300
N2—H20.889 (10)C8—C91.499 (3)
N3—O31.215 (2)C9—C141.384 (3)
N3—O21.216 (3)C9—C101.392 (3)
N3—C111.481 (3)C10—C111.378 (3)
O1—C81.232 (2)C10—H100.9300
C1—C61.395 (3)C11—C121.379 (3)
C1—C21.396 (3)C12—C131.379 (3)
C2—C31.397 (3)C12—H120.9300
C2—C71.463 (3)C13—C141.395 (3)
C3—C41.383 (3)C13—H130.9300
C3—H30.9300C14—H140.9300
C7—N1—N2116.89 (16)N1—C7—C2118.86 (18)
C8—N2—N1116.96 (15)N1—C7—H7120.6
C8—N2—H2122.3 (17)C2—C7—H7120.6
N1—N2—H2120.7 (17)O1—C8—N2123.05 (17)
O3—N3—O2123.7 (2)O1—C8—C9119.84 (17)
O3—N3—C11117.9 (2)N2—C8—C9117.11 (17)
O2—N3—C11118.37 (19)C14—C9—C10119.82 (18)
C6—C1—C2121.8 (2)C14—C9—C8123.54 (17)
C6—C1—Cl1117.98 (16)C10—C9—C8116.48 (17)
C2—C1—Cl1120.26 (16)C11—C10—C9118.99 (19)
C1—C2—C3117.44 (18)C11—C10—H10120.5
C1—C2—C7122.28 (19)C9—C10—H10120.5
C3—C2—C7120.28 (18)C10—C11—C12122.2 (2)
C4—C3—C2121.5 (2)C10—C11—N3118.0 (2)
C4—C3—H3119.2C12—C11—N3119.8 (2)
C2—C3—H3119.2C11—C12—C13118.4 (2)
C5—C4—C3119.0 (2)C11—C12—H12120.8
C5—C4—H4120.5C13—C12—H12120.8
C3—C4—H4120.5C12—C13—C14120.8 (2)
C6—C5—C4122.0 (2)C12—C13—H13119.6
C6—C5—Cl2119.02 (17)C14—C13—H13119.6
C4—C5—Cl2118.97 (19)C9—C14—C13119.8 (2)
C5—C6—C1118.3 (2)C9—C14—H14120.1
C5—C6—H6120.9C13—C14—H14120.1
C1—C6—H6120.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.89 (1)2.04 (2)2.859 (2)152 (2)
Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H9Cl2N3O3
Mr338.14
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.004 (3), 14.384 (3), 8.465 (2)
β (°) 96.302 (2)
V (Å3)1452.8 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.46
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.913, 0.921
No. of measured, independent and
observed [I > 2σ(I)] reflections		11555, 3163, 2128
Rint0.038
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.107, 1.05
No. of reflections3163
No. of parameters202
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.22, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.889 (10)2.042 (15)2.859 (2)152 (2)
Symmetry code: (i) x, −y+1/2, z+1/2.
 

Acknowledgements

We acknowledge the Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection for financial support (project No. JLCBE07026).

References

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3360
https://doi.org/10.1107/S1600536810049470
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